


Like... On a Date, Date?

by whenshewrites



Series: A Collection of One-Shots and Tumblr Prompts [80]
Category: Teen Wolf (TV)
Genre: Alpha Derek Hale, Derek Hale Deserves Nice Things, Derek Hale is Bad at Feelings, Derek Hale is Not a Failwolf, Fluff, Fluff and Humor, Idiots in Love, M/M, Mutual Pining, One Shot, Originally Posted on Tumblr, Pining, Pining Stiles Stilinski, Stiles Stilinski Is Bad at Feelings, Stiles Stilinski is a Little Shit, The Hale Pack - Freeform, The Pack Being Idiots, The Pack Ships It, Tumblr Prompt
Language: English
Status: Completed
Published: 2020-05-26
Updated: 2020-05-26
Packaged: 2021-03-02 19:42:13
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,810
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24392245
Author URL: https://archiveofourown.org/users/whenshewrites/pseuds/whenshewrites
Summary: Stiles just wants to ask out the Beacon Hills resident grumpy Alpha werewolf. But Derek doesn't make it easy.
Relationships: Derek Hale/Stiles Stilinski
Series: A Collection of One-Shots and Tumblr Prompts [80]
Series URL: https://archiveofourown.org/series/1956889
Comments: 27
Kudos: 583





	Like... On a Date, Date?

_ Right,  _ Stiles thought, there was nothing to it.  _ Go big or go home,  _ Scott had said, and it was as simple as that. Stiles wasn’t a coward— he was one hundred and forty-seven pounds of pale skin and fragile bone, but he wasn’t a coward. He could totally do this.

He faltered in front of the loft door, though, two cups of coffee in hand. Suddenly,  _ go big or go home  _ seemed like a bad idea. And he’d much rather go home.

But the door slid open before he could turn around and flee. An unimpressed Derek stood on the other side, one eyebrow raised in expectation. Stiles chuckled and shifted from foot to foot, offering his best innocent grin.

“Ah, Derek. Fancy seeing you here?”

“What.”

“Monosyllabic, I can tell we’re starting this morning with a bang,” Stiles said, skirting around the Alpha and plowing into the loft. Maybe if he talked fast enough and refused to back down, this could all be over before either one of them could blink.

Or before Derek could rip his throat out, at least. That too.

“Coffee,” Stiles said, turning toward Derek and shoving it into his hand. Derek took it with a confused expression and stared at the cup for a second, before giving Stiles a flat look. 

The man's hair was sticking up in random directions, Stiles realized, and he was wearing nothing but a pair of boxers and t-shirt. Stiles was pretty sure he hadn’t left the house that early— it’d been eight when his alarm clock went off. And by the time he escaped the coffee shop, it’d been nine. How long did big-bad Alphas sleep in on the weekend?

“What,” Derek said. “Is this?”

“Uh, coffee?”

“Why.”

“Well, clearly because you’re not a morning person,” Stiles said, moving to the couch and plopping down. He propped his feet up on the coffee table and took a nervous sip of his own drink. It was still too hot, stinging his tongue. Derek trailed after him, looking more than a little murderous.

“Stiles, what the hell are you doing in my loft?”

“Bringing coffee, Sourwolf, are we going to keep repeating this over and over again?”

_ “Why.” _

“Because,” Stiles said, wincing a little. “Go big or go home?”

Derek stared at him. Stiles sat up, setting his coffee on the table, and looked at the Alpha nervously. Once more, this seemed like a terrible idea. He should’ve come around lunch. Or dinner. Or literally any other time when Derek didn’t look like a sleep-deprived murderous teddy bear in his boxers _. _

“Look,” Stiles said, threading his fingers together. “We’re friends. Right?”

Derek stayed silent. Stiles swallowed.

“Um, yeah, we’re friends. And friends do friendly things, right? Like… get each other coffee sometimes or get breakfast on weekend mornings. Cause that’s, uh, what friends do. Do you know where I’m going with this?”

“I have no idea where you’re going with anything, ever,” Derek said flatly. Stiles winced.

“Do you want to get pancakes, Sourwolf? Or something?”

“Pancakes.”

“Yes.”

“Or something.”

“Yes, Sourwolf, this is how words work. Although usually, in a conversation, people  _ converse  _ back and forth, not repeat the same sentence over and over again like a broken record.”

Derek’s eyes flashed red. Stiles gulped.

“I meant that as nicely as possible. Broken records are great!”

Derek looked like he was torn between physically throwing Stiles out of the loft and sitting down to dwell on everything he’d just said. Stiles sighed and studied his face, accepting the fact this might take a little while. He should’ve known better than to listen to Scott. Of course, the puppy Alpha didn’t actually know  _ what  _ he was advising Stiles to do, but that was a problem for another time, was it not?

“You want to get breakfast,” Derek said after a moment. “With me.”

“Um. Yes?”

Derek looked like he wanted to ask  _ why  _ again and Stiles thought he might combust if the man did. Slowly, Derek sank into the seat opposite Stiles and just stared at him. Stiles licked his lips nervously, fighting the urge to get up and run.

“Stiles,” Derek said. He almost looked a little dumbfounded. “We’re… friends.”

_ Oh god, here we go again.  _ “Yes, Sourwolf.”

“And this is a friendly thing?”

Stiles narrowly resisted facepalming. He’d been working toward this for weeks— little things that he was pretty sure Derek had no idea about. Like dropping by at random times with a movie or dinner, or hanging out before or after training to ‘do homework’. 

He was pretty sure he was being stupid— dammit, he was pretty sure this crush was stupid— but if Stiles couldn’t woo the resident Alpha werewolf then he sure as hell was going to friendship the shit out of him. Whether Derek liked it or not.

“Yes,” Stiles said again. “Friendly, Derek. That’s this thing people do when they don’t actively hate each other.”

“With me.”

“Oh my god.”

“You’re both idiots,” a voice said behind him. Stiles squawked and spun around to see Erica plodding into the room with a tired-looking Boyd trailing after her. Erica’s hair was pulled up in curlers and she was wearing bright pink pajamas. Boyd was wearing nothing but sweatpants.

“Oh my god,” Stiles said, turning away. “You guys are here.”

“Yeah,” Erica said, snorting. “Or have you forgotten that we live here, idiot. Isaac is too, but he’s still asleep. Don’t worry, that pup can sleep through anything.”

“You’re here,” Stiles said again, his face turning hot. Derek was giving him a strange look and that wasn’t helping anyway. “Here. In the loft.”

“Now who’s the broken record?” Erica laughed. Stiles groaned, burying his face in his hands.

“I hate everything.”

“I really don’t understand you, Stiles,” Boyd said. Stiles lifted his head and winced when he realized Derek was still staring at him. He shot the dark-skinned beta a glare.

“Can you two leave. Please?”

“Why?” Erica asked, a smirk playing along the edges of her lips. “So you can ask Derek out in privacy? Because that clearly wasn’t working very well.”

_ Oh, shit. _

Derek’s face did a few things and he blinked, looking from Stiles, to Erica, and then back. Stiles was pretty sure if the floor was ever going to open up and swallow him whole, now would be the perfect time. But he’d never been so lucky.

“Ask me out?” Derek said, looking confused. “When?”

“You two are literally so helpless.”

“I wasn’t asking you out,” Stiles said quickly. “I was asking if we could get breakfast. As friends.”

“Right,” Erica said, laughter in her voice. “Friends with benefits?”

“Erica, shut up!”

Derek was looking at him strangely now. Stiles pushed himself up so hard, he shook the coffee table and his coffee went spilling. Tripping over his own feet, Stiles backtracked toward the door with his hands raised. Derek’s brows were drawn together; and Stiles figured he had at least thirty seconds before the Alpha actually figured things out.

“I’m just gonna— yeah, I’m gonna go— have a nice day!”

Erica called his name but Stiles ignored her, sliding the loft door open and then shut, leaning against it heavily. He blinked a few times and then shook his head, cursing himself.

_ Have a nice day? _

Stiles hated Scott. Things were never as simple as ‘go big or go home’.

He hurried down the hallway and could’ve sworn he heard the sound of the loft door opening again. Stiles stumbled down the stairs, sure if he moved fast enough he could make it to his jeep and be gone before Derek caught him. And then… and then they could never talk about this again.

Stiles was good with never talking about things again. And Derek never talked much in the first place.

Except, Stiles didn’t make it to his jeep. He was racing across the parking lot when his name echoed through the air and Stiles stumbled to a stop, freezing. He clenched his jaw and turned around to see Derek approaching,  _ still  _ only in his boxers and a t-shirt.

“Derek,” Stiles said. “I can explain.”

“Explain breakfast?”

“Yes. Wait, no. Maybe. How good of an explanation do you want?”

“Stiles,” Derek said, and it was in that  _ tone.  _ The one that made Stiles feel like he was twelve, not eighteen. The one that Derek always used when Stiles was being an idiot. And he wasn’t being an idiot right now, dammit.

“Don’t ‘Stiles’ me,” he said. “Just tell me you don’t see me that way and ‘we’re better off as friends’ and I promise everything can go back to normal. I won’t even look at you weird again.”

Derek blinked at him. Stiles crossed his arms, trying to smother his mix of hurt and embarrassment. 

“I wasn’t trying to be weird. I swear.”

“It wasn’t weird,” Derek said.

“I wasn’t trying to be creepy either. Just so you know.”

“It wasn’t creepy.

“Then, dammit, Derek, can we please pretend this never happened? Because I’m really good at doing that. Trust me, I’ve been rejected plenty of times before.”

“I’m not… trying to reject you,” Derek said slowly. Stiles blinked.

“What?”

Derek’s ears turned red and he shuffled his feet, not meeting Stiles’s gaze for the first time that morning. And suddenly, Stiles felt  _ different.  _ Emboldened, maybe. Go big or go home, right?

Dammit, Scott.

“Derek,” he said, stepping forward. “Will you get breakfast with me?”

“As friends?”

Stiles winced. “I mean, yeah it could be—”

“Or,” Derek said, cutting him off. “Dinner tonight. As… more?”

Stiles stared at him. Derek suddenly looked nervous.

“Or not.”

“Yes.”

“Yes?”

“Dinner,” Stiles said. “Now.”

“Now?”

“No,” Stiles said, shaking his head. “Not now. Tonight. As more. Not friends. But we could still get breakfast! Cause I’m starving. Also not as friends?”

Derek looked at him for a moment as if Stiles was a puzzle he couldn’t figure out. Then he glanced down at himself and looked back up at Stiles and said, “I’m in my boxers.”

And Stiles thought he was an idiot. But maybe Stiles was too. Because seriously— breakfast? Brunch was where it was at.

“Erica’s going to laugh at us,” he said. Derek glowered.

“She already has.”

“She’s going to do it again.”

“We could not go back inside at all?”

“You’re in your boxers,” Stiles reminded him, barely suppressing his snort of laughter. Derek’s ears turned red again.

“Drive through?”

Stiles grinned.  _ Right,  _ he thought, he was kind of awesome.  _ Go big or go home,  _ Scott had said, and it was as simple as that. And this? Stiles was one hundred and forty-seven pounds of pale skin and fragile bone, and he was going to get drive-through breakfast. With Derek Hale.

“Drive through,” he said, Derek’s face softening in relief.  _ And not as friends. _

_ Take that, Erica. _

**Author's Note:**

> Written for the prompt; "go big or go home" and I had so much fun! I hope you all enjoyed and hope you're all staying safe. The comments and support you guys leave makes my day!
> 
> Come hang with me on Tumblr! 
> 
> [tumblr dumpser](https://when-she-writes-stuff.tumblr.com/)


End file.
